CN1269817C - 脱卤代化合物 - Google Patents
脱卤代化合物 Download PDFInfo
- Publication number
- CN1269817C CN1269817C CNB018220746A CN01822074A CN1269817C CN 1269817 C CN1269817 C CN 1269817C CN B018220746 A CNB018220746 A CN B018220746A CN 01822074 A CN01822074 A CN 01822074A CN 1269817 C CN1269817 C CN 1269817C
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- Prior art keywords
- cyclopropyl
- salt
- hydrate
- amino
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 251
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 57
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 230000001225 therapeutic effect Effects 0.000 claims description 7
- CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical compound O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 claims description 6
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- 239000002904 solvent Substances 0.000 description 38
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 35
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 20
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical class C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 19
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- 239000002585 base Substances 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 17
- 230000002378 acidificating effect Effects 0.000 description 17
- 230000000845 anti-microbial effect Effects 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 125000006239 protecting group Chemical group 0.000 description 16
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 16
- 201000010099 disease Diseases 0.000 description 15
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 239000000523 sample Substances 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
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- 125000003342 alkenyl group Chemical group 0.000 description 12
- 235000001014 amino acid Nutrition 0.000 description 12
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- 239000003242 anti bacterial agent Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP352269/2000 | 2000-11-20 | ||
| JP352269/00 | 2000-11-20 | ||
| JP2000352269 | 2000-11-20 | ||
| JP248822/01 | 2001-08-20 | ||
| JP2001248822 | 2001-08-20 | ||
| JP248822/2001 | 2001-08-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1486315A CN1486315A (zh) | 2004-03-31 |
| CN1269817C true CN1269817C (zh) | 2006-08-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB018220746A Expired - Fee Related CN1269817C (zh) | 2000-11-20 | 2001-11-19 | 脱卤代化合物 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20040063754A1 (ja) |
| EP (1) | EP1336611B1 (ja) |
| JP (3) | JP3711108B2 (ja) |
| KR (1) | KR100777149B1 (ja) |
| CN (1) | CN1269817C (ja) |
| AR (1) | AR035599A1 (ja) |
| AT (1) | ATE372338T1 (ja) |
| AU (1) | AU2405002A (ja) |
| BR (1) | BR0115326A (ja) |
| CA (1) | CA2429440C (ja) |
| DE (1) | DE60130359T2 (ja) |
| ES (1) | ES2292642T3 (ja) |
| HK (1) | HK1056729A1 (ja) |
| IL (2) | IL155976A0 (ja) |
| MX (1) | MXPA03004437A (ja) |
| MY (1) | MY136916A (ja) |
| NO (1) | NO326157B1 (ja) |
| PT (1) | PT1336611E (ja) |
| TW (1) | TWI315308B (ja) |
| WO (1) | WO2002040478A1 (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2429440C (en) | 2000-11-20 | 2009-12-29 | Daiichi Pharmaceutical Co., Ltd. | Dehalogeno-compounds |
| JP4675234B2 (ja) * | 2003-06-06 | 2011-04-20 | 第一三共株式会社 | 光学活性なキノロンカルボン酸誘導体の製造中間体およびその製造法 |
| WO2004113321A1 (ja) * | 2003-06-19 | 2004-12-29 | Daiichi Pharmaceutical Co., Ltd. | 選択的なアミノ置換基導入法 |
| JP4629973B2 (ja) * | 2003-09-22 | 2011-02-09 | 第一三共株式会社 | 光学活性シクロプロピルアミン誘導体およびその製造方法 |
| WO2005030752A1 (ja) * | 2003-09-29 | 2005-04-07 | Daiichi Pharmaceutical Co., Ltd. | ８−シアノキノロンカルボン酸誘導体 |
| ES2537976T3 (es) | 2003-12-12 | 2015-06-16 | Daiichi Sankyo Company, Limited | Compuestos intermedios para la producción de derivados de ciclopropilamina ópticamente activos y procedimiento para la producción de los compuestos intermedios |
| RU2007104026A (ru) * | 2004-07-02 | 2008-08-10 | Дайити Фармасьютикал Ко., Лтд. (JP) | Содержащая хинолон лекарственная композиция |
| TW200744598A (en) * | 2005-09-28 | 2007-12-16 | Daiichi Seiyaku Co | Process for the production of freeze-dried preparations containing quinolones |
| CN100441580C (zh) * | 2006-07-14 | 2008-12-10 | 中山大学 | 喹啉二酮衍生物及其在制备抗菌药物中的应用 |
| KR101502453B1 (ko) * | 2006-08-11 | 2015-03-24 | 노던 안티바이오틱스 리미티드 | 폴리믹신 유도체들 및 이들의 용도 |
| JP5174365B2 (ja) * | 2007-03-23 | 2013-04-03 | 第一三共株式会社 | キノロン含有凍結乾燥製剤の製造方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0207420B1 (en) * | 1985-06-26 | 1992-05-06 | Daiichi Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives |
| DE69531305T2 (de) * | 1994-10-20 | 2004-05-13 | Wakunaga Seiyaku K.K. | Pyridoncarboxylat- derivate oder salze davon und antibakterielle zusammensetzungen die diese als aktiven bestandteil enthalten |
| CA2212007C (en) * | 1995-02-02 | 2004-09-14 | Daiichi Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives substitued by a bicyclic amino group |
| EP0992501B1 (en) * | 1995-09-22 | 2002-08-28 | Wakunaga Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivatives as antibacterial agents |
| CN1119343C (zh) | 1995-11-22 | 2003-08-27 | 第一制药株式会社 | 取代的氨基环烷基吡咯烷衍生物 |
| US6121285A (en) * | 1995-11-22 | 2000-09-19 | Daiichi Pharmaceutical Co., Ltd. | Substituted aminocycloalkylpyrrolidine derivatives and cis-substituted aminocycloalkylpyrrolidine derivatives |
| US6391889B2 (en) * | 1996-07-12 | 2002-05-21 | Daiichi Pharmaceutical Co., Ltd. | Cis-substituted aminocyclopropane derivatives |
| JPH1081682A (ja) | 1996-07-12 | 1998-03-31 | Dai Ichi Seiyaku Co Ltd | シス置換アミノシクロプロパン誘導体 |
| TW519542B (en) * | 1996-09-27 | 2003-02-01 | Daiichi Seiyaku Co | Bicyclic amine derivative |
| IL132982A0 (en) * | 1997-05-21 | 2001-03-19 | Daiichi Seiyaku Co | Cis-disubstituted aminocycloalkyl-pyrrolidine derivatives |
| MY119816A (en) | 1997-05-30 | 2005-07-29 | Daiichi Seiyaku Co | Substituted cyclobutylamine derivatives |
| KR20010014209A (ko) * | 1997-06-24 | 2001-02-26 | 스즈키 다다시 | 시스-치환된 플루오로메틸피롤리딘 유도체 |
| HUP0100051A3 (en) * | 1997-09-15 | 2002-08-28 | Procter & Gamble | Antimicrobial quinolones, their compositions and uses |
| JP2000023709A (ja) * | 1998-07-16 | 2000-01-25 | Shimano Inc | 長 靴 |
| DE19834202A1 (de) | 1998-07-29 | 2000-02-10 | Coherent Luebeck Gmbh | Rauscharmer frequenzvervielfachter Laser mit Strahlseparator |
| ATE297912T1 (de) | 1998-11-24 | 2005-07-15 | Daiichi Seiyaku Co | Cycloalkylsubstituierte aminomethylpyrrolidin- derivate |
| CA2429440C (en) | 2000-11-20 | 2009-12-29 | Daiichi Pharmaceutical Co., Ltd. | Dehalogeno-compounds |
-
2001
- 2001-11-19 CA CA002429440A patent/CA2429440C/en not_active Expired - Fee Related
- 2001-11-19 AU AU2405002A patent/AU2405002A/xx not_active Withdrawn
- 2001-11-19 BR BR0115326-9A patent/BR0115326A/pt active Search and Examination
- 2001-11-19 PT PT01996540T patent/PT1336611E/pt unknown
- 2001-11-19 DE DE60130359T patent/DE60130359T2/de not_active Expired - Lifetime
- 2001-11-19 AR ARP010105401A patent/AR035599A1/es active IP Right Grant
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